Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines.

Abstract:

:Diacylhydrazine derivatives have been identified as one of the most important insect growth regulators. A variety of diacylhydrazine derivatives were designed and synthesized in recent years due to their unique action mechanism, simple structure, and environmental benign character. This paper describes the molecular design, synthesis, and insecticidal activities of a series of chromanone and chromone analogues of diacylhydrazine derivatives. The preliminary bioassay showed that some of the chromanone analogues exhibited good insecticidal activity against Mythima separata at the dosage of 500 mg L-1. The present work demonstrated that replacement of the chroman ring of ANS-118, a commercial insecticide, with chromanone moiety could result in new compounds with high potent insecticidal activity.

journal_name

Bioorg Med Chem

authors

Zhao PL,Li J,Yang GF

doi

10.1016/j.bmc.2007.01.008

subject

Has Abstract

pub_date

2007-03-01 00:00:00

pages

1888-95

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00023-5

journal_volume

15

pub_type

杂志文章
  • Preparation and biological properties of biotinylated PhTX derivatives.

    abstract::We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00054-1

    authors: Hashimoto M,Liu Y,Fang K,Li HY,Campiani G,Nakanishi K

    更新日期:1999-06-01 00:00:00

  • Structure-activity relationship studies of manzamine A: amidation of positions 6 and 8 of the beta-carboline moiety.

    abstract::Twenty manzamine amides were synthesized and evaluated for in vitro antimalarial and antimicrobial activities. The amides of manzamine A (1) showed significantly reduced cytotoxicity against Vero cells, although were less active than 1. The structure-activity analysis showed that linear, short alkyl groups adjacent to...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.09.026

    authors: Wahba AE,Peng J,Kudrimoti S,Tekwani BL,Hamann MT

    更新日期:2009-11-15 00:00:00

  • Inhibition of the Ser-Thr phosphatases PP1 and PP2A by naturally occurring toxins.

    abstract::The okadaic acid class of naturally occurring toxins is a structurally diverse group of molecules that inhibit the protein phosphatases PP1 and PP2A. Studies providing information about the mode of binding between the toxins and the phosphatases contribute to an overall understanding of the signal transduction pathway...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0968-0896(97)00146-6

    authors: Sheppeck JE 2nd,Gauss CM,Chamberlin AR

    更新日期:1997-09-01 00:00:00

  • Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials.

    abstract::Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.051

    authors: Xiao ZP,He XB,Peng ZY,Xiong TJ,Peng J,Chen LH,Zhu HL

    更新日期:2011-03-01 00:00:00

  • Dose dependent actions of LCL521 on acid ceramidase and key sphingolipid metabolites.

    abstract::The function of acid ceramidase (ACDase), whose congenital deficiency leads to Farber disease, has been recognized to be vital to tumor cell biology, and inhibition of its activity may be beneficial in cancer therapy. Therefore, manipulation of the activity of this enzyme may have significant effect, especially on can...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.11.012

    authors: Bai A,Bielawska A,Rahmaniyan M,Kraveka JM,Bielawski J,Hannun YA

    更新日期:2018-12-15 00:00:00

  • Inhibition of secreted phospholipases A₂ by 2-oxoamides based on α-amino acids: Synthesis, in vitro evaluation and molecular docking calculations.

    abstract::Group IIA secreted phospholipase A₂ (GIIA sPLA₂) is a member of the mammalian sPLA₂ enzyme family and is associated with various inflammatory conditions. In this study, the synthesis of 2-oxoamides based on α-amino acids and the in vitro evaluation against three secreted sPLA₂s (GIIA, GV and GX) are described. The lon...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.12.030

    authors: Mouchlis VD,Magrioti V,Barbayianni E,Cermak N,Oslund RC,Mavromoustakos TM,Gelb MH,Kokotos G

    更新日期:2011-01-15 00:00:00

  • Identification and development of the 1,4-benzodiazepin-2-one and quinazoline-2,4-dione scaffolds as submicromolar inhibitors of HAT.

    abstract::A library of 1,4-benzodiazepines has been synthesised and evaluated for activity against Trypanosoma brucei, a causative parasite of Human African Trypanosomiasis (HAT). The most potent of these derivatives has an MIC value of 0.97 μM. Herein we report the design, synthesis and biological evaluation of the abovementio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.08.049

    authors: Clark RL,Clements CJ,Barrett MP,Mackay SP,Rathnam RP,Owusu-Dapaah G,Spencer J,Huggan JK

    更新日期:2012-10-15 00:00:00

  • Chemical synthesis and biochemical characterization of cyclic oligonucleotides containing acyl groups at both 5'- and 3'-terminal positions.

    abstract::Modified oligonucleotides, whose ON-OFF switch of hybridization can be controlled by an external stimulus, are important to understanding life phenomena and efficient treatment of diseases. The ON-OFF switch can be completely controlled by chemical modification of the oligonucleotide such as cyclization. However, thei...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115799

    authors: Nishizawa S,Ohkubo A

    更新日期:2020-12-01 00:00:00

  • Synthesis of new analogs of AKBA and evaluation of their anti-inflammatory activities.

    abstract::A new series of 11-keto-β-boswellic acid and 3-O-acetyl-11-keto-β-boswellic acid analogs (5, 7, 8, 10, 13, 18a-d, 27a-c, 28a-d) were synthesized by modification of hydroxyl and acid functional moieties of boswellic acids. The structures of these analogs were confirmed by spectral data analysis (1H, 13C NMR and mass). ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.12.045

    authors: Meka B,Ravada SR,Murali Krishna Kumar M,Purna Nagasree K,Golakoti T

    更新日期:2017-02-15 00:00:00

  • Benzhydrylquinazolinediones: novel cytosolic phospholipase A2alpha inhibitors with improved physicochemical properties.

    abstract::The synthesis and optimization of a class of trisubstituted quinazoline-2,4(1H,3H)-dione cPLA(2)alpha inhibitors are described. Utilizing pharmacophores that were found to be important in our indole series, we discovered inhibitors with reduced lipophilicity and improved aqueous solubility. These compounds are active ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.05.027

    authors: Kirincich SJ,Xiang J,Green N,Tam S,Yang HY,Shim J,Shen MW,Clark JD,McKew JC

    更新日期:2009-07-01 00:00:00

  • Synthesis, in vitro and in vivo preliminary evaluation of anti-angiogenic properties of some pyrroloazaflavones.

    abstract::This work investigated the in vitro and in vivo anti-angiogenic activity of some pyrroloazaflavones, exactly 2-phenyl-1H-pyrrolo[2,3-h]quinolin-4(7H)ones, with vinblastine as reference compound. Growth inhibitory activity, migration, and capillary-like structures formation were determined in human umbilical vein endot...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.11.010

    authors: Ferlin MG,Conconi MT,Urbani L,Oselladore B,Guidolin D,Di Liddo R,Parnigotto PP

    更新日期:2011-01-01 00:00:00

  • Selective activity against Mycobacteriumtuberculosis of new quinoxaline 1,4-di-N-oxides.

    abstract::New series of 3-phenylquinoxaline 1,4-di-N-oxide with selective activity against Mycobacterium tuberculosis have been prepared and evaluated. Thirty-four of the seventy tested compounds showed an MIC value less than 0.2 microg/mL, a value on the order of the MIC of rifampicin. Furthermore, 45% of the evaluated derivat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.086

    authors: Vicente E,Pérez-Silanes S,Lima LM,Ancizu S,Burguete A,Solano B,Villar R,Aldana I,Monge A

    更新日期:2009-01-01 00:00:00

  • Benzimidazole inhibitors from the Niclosamide chemotype inhibit Wnt/β-catenin signaling with selectivity over effects on ATP homeostasis.

    abstract::The Wnt signaling pathway plays a key role in organ and tissue homeostasis, and when dysregulated, can become a major underlying mechanism of disease, particularly cancer. We reported previously that the anthelmintic drug Niclosamide inhibits Wnt/β-catenin signaling and suppresses colon cancer cell growth in vitro and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.01.046

    authors: Mook RA Jr,Ren XR,Wang J,Piao H,Barak LS,Kim Lyerly H,Chen W

    更新日期:2017-03-15 00:00:00

  • Development of water-soluble 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents.

    abstract::In this work, four series of tertiary amine-containing derivatives of 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents were prepared, and their in vitro antimycobacterial effects were evaluated. We found that the studied compounds showed lipophilicity-dependent antimycobacterial activity. The N-benzylp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.08.010

    authors: Roh J,Karabanovich G,Vlčková H,Carazo A,Němeček J,Sychra P,Valášková L,Pavliš O,Stolaříková J,Klimešová V,Vávrová K,Pávek P,Hrabálek A

    更新日期:2017-10-15 00:00:00

  • Systematic synthesis of N-methyl-1-deoxynojirimycin-containing, Le(x), Le(a), sialyl-Le(x) and sialyl-Le(a) epitopes recognized by selectins.

    abstract::A systematic synthesis of the N-methyl-1-deoxynojirimycin-containing oligosaccharides related to the Lewis x, Lewis a, sialyl-Lewis x and sialyl-Lewis a antigens has been achieved. The couplings of the suitably protected 1-deoxynojirimycin derivative 10 with methyl-1-thioglycosides (glycosyl donors) of L-fucose (11), ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)82080-5

    authors: Kiso M,Furui H,Ando K,Ishida H,Hasegawa A

    更新日期:1994-11-01 00:00:00

  • Effects of sesquiterpenes and amino acid-sesquiterpene conjugates from the roots of Saussurea lappa on inducible nitric oxide synthase and heat shock protein in lipopolysaccharide-activated macrophages.

    abstract::The methanolic extract of the roots of Saussurea lappa CLARKE, a Chinese medicinal herb Saussureae Radix, was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. Among the constituents from the methanolic extract, two sesquiterpene lactones (costunolide and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00471-6

    authors: Matsuda H,Toguchida I,Ninomiya K,Kageura T,Morikawa T,Yoshikawa M

    更新日期:2003-03-06 00:00:00

  • Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin.

    abstract::All eight stereoisomers of saxagliptin have been synthesized and evaluated for their inhibitory activity against DPP-IV. It was unambiguously confirmed that the configuration of saxagliptin was critical to potent inhibition of DPP-IV. Docking study was performed to elucidate the configuration-activity relationship of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.12.061

    authors: Dong J,Gong Y,Liu J,Chen X,Wen X,Sun H

    更新日期:2014-02-15 00:00:00

  • Discovery of novel quinoline-based mTOR inhibitors via introducing intra-molecular hydrogen bonding scaffold (iMHBS): The design, synthesis and biological evaluation.

    abstract::A series of quinoline derivatives featuring the novelty of introducing intra-molecular hydrogen bonding scaffold (iMHBS) were designed, synthesized and biologically evaluated for their mTOR inhibitory activity, as well as anti-proliferative efficacies against HCT-116, PC-3 and MCF-7 cell lines. As a result, six compou...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.11.003

    authors: Ma X,Lv X,Qiu N,Yang B,He Q,Hu Y

    更新日期:2015-12-15 00:00:00

  • Antimicrobial and cytotoxic arylazoenamines. Part III: antiviral activity of selected classes of arylazoenamines.

    abstract::Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses. The most commonly affected viruses were, in decreasing order, CVB-2, RSV, BVDV, YFV, and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.028

    authors: Tonelli M,Boido V,Canu C,Sparatore A,Sparatore F,Paneni MS,Fermeglia M,Pricl S,La Colla P,Casula L,Ibba C,Collu D,Loddo R

    更新日期:2008-09-15 00:00:00

  • Chiral switch of enzymatic ketone reduction by addition of gamma-cyclodextrin.

    abstract::We report a chiral switch in the configuration of 1-(p-methoxyphenyl)-propan-2-ol, synthesized in aqueous media by ketoreductase in the presence of high concentration of gamma-CD. NMR, ECD and fluorescence spectrometry were used in the effort to explain this unexpected effect. A comparison has been made between the ca...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.07.070

    authors: Petkova GA,Král V

    更新日期:2010-09-15 00:00:00

  • Medicinal attributes of pyrazolo[3,4-d]pyrimidines: a review.

    abstract::Pyrazolopyrimidines are the fused heterocyclic ring systems which structurally resemble purines which prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The advent of their first bioactivity as adenosine antagonis...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2013.07.027

    authors: Chauhan M,Kumar R

    更新日期:2013-09-15 00:00:00

  • Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.

    abstract::A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of beta-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemag...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.06.009

    authors: Lewin AH,Navarro HA,Mascarella SW

    更新日期:2008-08-01 00:00:00

  • The chemistry and biology of febrifugine and halofuginone.

    abstract::The trans-2,3-disubstituted piperidine, quinazolinone-containing natural product febrifugine (also known as dichroine B) and its synthetic analogue, halofuginone, possess antimalarial activity. More recently studies have also shown that halofuginone acts as an agent capable of reducing fibrosis, an indication with cli...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2014.02.040

    authors: McLaughlin NP,Evans P,Pines M

    更新日期:2014-04-01 00:00:00

  • C-2-aryl O-substituted HI-236 derivatives as non-nucleoside HIV-1 reverse-transcriptase inhibitors.

    abstract::Several novel thiourea derivatives of the NNRTI HI-236 substituted at the C-2 oxygen of the phenyl ring have been synthesized and evaluated for their inhibitory activity against HIV-1 (IIIB) replication in MT-2 cell cultures. The compounds were synthesized in order to fine-tune the activity of HI-236 as well as to gai...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.048

    authors: Hunter R,Younis Y,Muhanji CI,Curtin TL,Naidoo KJ,Petersen M,Bailey CM,Basavapathruni A,Anderson KS

    更新日期:2008-12-15 00:00:00

  • A new class of non-thiazolidinedione, non-carboxylic-acid-based highly selective peroxisome proliferator-activated receptor (PPAR) γ agonists: design and synthesis of benzylpyrazole acylsulfonamides.

    abstract::Herein, we describe the design, synthesis, and structure-activity relationships of novel benzylpyrazole acylsulfonamides as non-thiazolidinedione (TZD), non-carboxylic-acid-based peroxisome proliferator-activated receptor (PPAR) γ agonists. Docking model analysis of in-house weak agonist 2 bound to the reported PPARγ ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.008

    authors: Rikimaru K,Wakabayashi T,Abe H,Imoto H,Maekawa T,Ujikawa O,Murase K,Matsuo T,Matsumoto M,Nomura C,Tsuge H,Arimura N,Kawakami K,Sakamoto J,Funami M,Mol CD,Snell GP,Bragstad KA,Sang BC,Dougan DR,Tanaka T,Katayama

    更新日期:2012-01-15 00:00:00

  • Discovery of melanin-concentrating hormone receptor R1 antagonists using high-throughput synthesis.

    abstract::A structure-activity study on benzylpiperidine 1 was accomplished by utilizing high-throughput synthesis. Three focused libraries were designed and synthesized to quickly develop SAR. Further optimization led to the discovery of compound 2, an MCH receptor R1 antagonist with over 400-fold improvement in biological act...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.11.046

    authors: Su J,McKittrick BA,Tang H,Czarniecki M,Greenlee WJ,Hawes BE,O'Neill K

    更新日期:2005-03-01 00:00:00

  • Discovery and structure activity relationship of the first potent cryptosporidium FIKK kinase inhibitor.

    abstract::FIKKs are parasite-specific protein kinases with distinctive sequence motifs and their biological roles have not been completely elucidated. Here, we report the first potent Cryptosporidium FIKK (CpFIKK) inhibitor. We identified 4b as a potent (IC50=0.2nM) inhibitor of CpFIKK catalytic activity. In addition, we identi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.01.036

    authors: Osman KT,Ye J,Shi Z,Toker C,Lovato D,Jumani RS,Zuercher W,Huston CD,Edwards AM,Lautens M,Santhakumar V,Hui R

    更新日期:2017-03-01 00:00:00

  • Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6beta-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents.

    abstract::A codrug approach for simultaneous treatment of alcohol abuse and tobacco dependence is considered as very desirable because of substantial evidence that smoking is increased significantly during drinking, and that smoking is regarded as a behavioral 'cue' for the urge to consume alcohol. The purpose of this study was...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.06.018

    authors: Hamad MO,Kiptoo PK,Stinchcomb AL,Crooks PA

    更新日期:2006-10-15 00:00:00

  • Tools and methodologies capable of isolating and identifying a target molecule for a bioactive compound.

    abstract::Elucidating the mechanism of action of bioactive compounds, such as commonly used pharmaceutical drugs and biologically active natural products, in the cells and the living body is important in drug discovery research. To this end, isolation and identification of target protein(s) for the bioactive compound are essent...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.022

    authors: Sakamoto S,Hatakeyama M,Ito T,Handa H

    更新日期:2012-03-15 00:00:00

  • Structure-based design and discovery of novel inhibitors of protein tyrosine phosphatases.

    abstract::Protein tyrosine phosphatases (PTPs) are important in the regulation of signal transduction processes. Certain enzymes of this class are considered as potential therapeutic targets in the treatment of a variety of diseases such as diabetes, inflammation, and cancer. However, many PTP inhibitors identified to date are ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00039-7

    authors: Huang P,Ramphal J,Wei J,Liang C,Jallal B,McMahon G,Tang C

    更新日期:2003-04-17 00:00:00